In earlier work we had shown that a strain of the mold Rhizopus nigricans could be used to enantioselectively hydrolyze a variety of racemic acetates. We suggested a model which enabled one to rationalize these results and have investigated the hydrolyses of several series of compounds in order to compare the experimental results with predictions made using the model. In a series of acyclic esters replacing hydrogens on the methylene adjacent to the carbinol carbon by one, two or three methyl groups, or by a chlorine atom, did not change the configuration of the carbinol formed. However, in two series of cyclic esters (1-indanyl and 1-tetralyl acetate), replacement of the trans-methylene hydrogen by a variety of substituents always inverted the configuration of the carbinol formed. Several mono- and di-methyl derivatives of 1,2-indane oxide and 1,2,3,4-tetra-hydro-1,2-naphthalene oxide have been prepared. The 1-methyl derivatives were found to undergo a lithium catalyzed rearrangement to form allylic alcohols, while the 2-substituted compounds were unreactive under the same conditions. Unsubstituted 1, 2-indane oxide and 1,2,3,4-tetrahydro-1,2-naphthalene oxide rearranged to 2-indanone and 2-tetralone when reacted with lithium salts.